2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester

Base Information

• Chemical Name: 2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester
• CAS No.: 834916-92-6
• Molecular Formula: C₅₁H₁₀₂O₉Si₃
• Molecular Weight: 943.622

Synonyms:2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester

Chemical Property of 2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester

There total 15 articles about 2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

triethylsilyl chloride (994-30-9) → 2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester (834916-92-6)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / dimethylformamide / 20 °C

2: DIBAL-H / toluene / -78 °C

3: SO₃*py; Et₃N; DMSO / CH₂Cl₂ / 20 °C

4: tetrahydrofuran / 0 °C

5: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

6: 95 percent / tetrahydrofuran / 20 °C

7: tetrahydrofuran / 20 °C

8: aq. H₂O₂; NaOH / 0 - 20 °C

9: DMAP; pyridine / 20 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; pyridine-SO₃ complex; dihydrogen peroxide; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Dess-Martin oxidation;

DOI:10.1002/anie.200461802

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester (834916-92-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 91 percent / Na; liq. NH₃ / tetrahydrofuran / -78 °C

3: pyridine / 20 °C

4: imidazole / dimethylformamide / 20 °C

5: DIBAL-H / toluene / -78 °C

6: SO₃*py; Et₃N; DMSO / CH₂Cl₂ / 20 °C

7: tetrahydrofuran / 0 °C

8: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

9: 95 percent / tetrahydrofuran / 20 °C

10: tetrahydrofuran / 20 °C

11: aq. H₂O₂; NaOH / 0 - 20 °C

12: DMAP; pyridine / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; pyridine-SO₃ complex; ammonia; dihydrogen peroxide; sodium; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 8: Dess-Martin oxidation;

DOI:10.1002/anie.200461802

Reference yield:

(1R,2S)-1-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-2-[(S)-hydroxy-((2R,4S,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-methyl]-4-methoxymethoxymethyl-cyclohex-3-enecarbonitrile (834916-83-5) → 2,2-dimethyl-propionic acid 2-{6-[6-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester (834916-92-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 88 percent / CSA / CH₂Cl₂ / 20 °C

2.1: DIBAL-H / toluene / -30 - 20 °C

2.2: SiO₂ / hexane / 20 °C

2.3: DIBAL-H / toluene / -78 - 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

4.1: 91 percent / Na; liq. NH₃ / tetrahydrofuran / -78 °C

5.1: pyridine / 20 °C

6.1: imidazole / dimethylformamide / 20 °C

7.1: DIBAL-H / toluene / -78 °C

8.1: SO₃*py; Et₃N; DMSO / CH₂Cl₂ / 20 °C

9.1: tetrahydrofuran / 0 °C

10.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

11.1: 95 percent / tetrahydrofuran / 20 °C

12.1: tetrahydrofuran / 20 °C

13.1: aq. H₂O₂; NaOH / 0 - 20 °C

14.1: DMAP; pyridine / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; pyridine-SO₃ complex; camphor-10-sulfonic acid; ammonia; dihydrogen peroxide; sodium; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 10.1: Dess-Martin oxidation;

DOI:10.1002/anie.200461802

upstream raw materials:

triethylsilyl chloride

t-butyldimethylsiyl triflate

(1R,2S)-1-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-2-[(S)-hydroxy-((2R,4S,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-methyl]-4-methoxymethoxymethyl-cyclohex-3-enecarbonitrile

(1R,2S)-2-((4S,4aS,6R,8aR)-2,2-Dimethyl-6-phenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-1-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-4-methoxymethoxymethyl-cyclohex-3-enecarbonitrile

Downstream raw materials:

2,2-Dimethyl-propionic acid (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-6-formyl-3-methoxymethoxymethyl-cyclohex-2-enyl]-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl}-propyl ester

2,2-Dimethyl-propionic acid (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-6-formyl-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester

(R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol

(R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((R)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol

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